title: Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection-macrocyclisation approach.
abstract: A solid-phase total synthesis of integerrimide A (1) is reported. This work employs a safety-catch linker which enables head-to-tail cyclisation of the required linear peptide 6 as a method of cleaving the peptide from the solid support, and highlights a new tandem approach to direct macrocyclisation. It provides access to useful quantities of 1 in 16 steps and 19% overall yield, based on the manufacturer's stated resin substitution from commercially available materials, and also verifies the absolute stereochemistry of the natural product.
authors.affiliation: Institute of Molecular Biosciences, Mahidol University, 25/25, Phuttamonthon 4 Road, Salaya, Nakhon Pathom, 73170, Thailand. sirirat.kum@mahidol.ac.th.
authors.forename: Sirirat
authors.initials: S
authors.lastname: Kumarn
authors.forename: Nitirat
authors.initials: N
authors.lastname: Chimnoi
authors.forename: Somsak
authors.initials: S
authors.lastname: Ruchirawat
mesh_terms: D003500:Cyclization; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques
chemical_list: D010456:Peptides, Cyclic; C515180:integerrimide A